Xyloccensins O and P, Unique 8,9,30-Phragmalin Ortho Esters from Xylocarpus granatum

Abstract

Two unique 8,9,30-phragmalin ortho esters, xyloccensins O (1) and P (2), were isolated from the mangrove plant Xylocarpus granatum. They are a new type of ortho ester of phragmalin. The structures were determined by spectroscopic and single-crystal X-ray diffraction techniques. The biogenetic pathway to these new phragmalins was also proposed. [structure: see text]

Xyloccensins X1 and X2, Two New Mexicanolides from the Fruit of a Chinese Mangrove Xylocarpus granatum

“…Mexicanolide, a tetranortriterpene with a characteristic bicyclo[3.3.1 2,10 ]nonane ring system, was isolated from Khaya grandifoliola and its structure was determined by single-crystal X-ray diffraction analysis [1]. To date, many mexicanolides showing antifeedant and antifungal activities have been reported from meliaceae plants [2 -7].…”

Limonoids and Tirucallane Derivatives from the Seeds of a Krishna Mangrove, Xylocarpus moluccensis

“…[10][11][12] To date, 42 mexicanolides and 23 phragmalins, including three 1,8,9-phragmalin ortho esters, eight 8,9,30-phragmalin ortho esters, and 12 polyhydroxylated phragmalins, have been isolated from the wood, seeds, and fruits of X. granatum and X. moluccensis. 13 We recently identified seven phragmalins, moluccensins A-G, 14 from seeds of an Indian mangrove, X. moluccensis, collected in the mangrove wetlands of Krishna estuary, Andhra…”

“…They are classified by the type of foursusually highly oxidizedsrings (designated as A, B, C, and D) in the intact triterpene. Phragmalins, such as pseudrelones A 1 and A 2 1 isolated from Pseudocedrela kotschyii and khayanolides A-C 2 from Khaya senegalensis, have characteristic tricyclo[3.3.1 2,10 .1 1,4 ]decane or tricyclo[4.2.1 10,30 .1 1,4 ]decane ring systems. The family Meliaceae has proved to produce a variety of antifeedant limonoids, such as azadirachtin 3 from the neem tree, Azadiracha indica, and harrisonin 4 from Harrisonnia abyssinica.…”

“…M Roem. (Meliaceae), together with two new andirobin-type limonoids (7,8), two new tirucallane derivatives (9,10), and the known compound 3 ,22S-dihydroxytirucalla-7,24-dien-23-one. 15 The structures of these compounds were established on the basis of spectroscopic data or comparison with data in the literature.…”

Khayasin and 2'S-methylbutanoylproceranolide: Promising candidate insecticides for the control of the coconut leaf beetle, Brontispa longissima

“…[6][7][8] To date, 42 mexicanolides and 23 phragmalins have been isolated from the wood, seeds, and fruits of X. granatum and X. moluccensis. 9) In this paper, we present the isolation and characterization of khayasin (1) and 2ЈS-methylbutanoylproceranolide (2) (Fig.…”